Ethanol → Ethyl 2-(4-((dimethylamino)methyl)phenyl)-3-(4-ethylphenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968133ノート

反応式

HRID 1968133 の反応式
[CH3:1][N:2]([CH2:4][C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[N:10]/[C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][O:14][C:15]3=[O:20])=[CH:7][CH:6]=1)[CH3:3].[CH2:23]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)[CH3:24].[O-:33][CH2:34][CH3:35].[Na+].C(O)C>C(OCC)(=O)CC>[CH3:1][N:2]([CH2:4][C:5]1[CH:22]=[CH:21][C:8]([CH:9]2[CH:29]([C:28]3[CH:31]=[CH:32][C:25]([CH2:23][CH3:24])=[CH:26][CH:27]=3)[C:34](=[O:33])[C:35]3[C:16]([C:15]([O:14][CH2:13][CH3:12])=[O:20])=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10]2)=[CH:7][CH:6]=1)[CH3:3]

参加物

6

反応物 4

HCID 702EthanolHCID 208614-EthylbenzaldehydeHCID 2723922Sodium ethoxideHCID 178483208HCID 178483208、化合物

生成物 1

HCID 67258510Ethyl 2-(4-((dimethylamino)methyl)phenyl)-3-(4-ethylphenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate収率 32%

試薬・触媒・溶媒 1

HCID 7749Ethyl Propionate溶媒

反応条件

温度
0 °C

実験手順

A mixture of (E)-4-(4-((dimethylamino)methyl)benzylideneamino)isobenzofuran-1(3H)-one (588 mg, 2 mmol) and 4-ethylbenzaldehyde (268 mg, 2 mmol) in ethyl propionate (15 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (138 mg, 6 mmol) in ethanol (5 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 3 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (100 mL×4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product, which was purified by chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give the crude title compound (290 mg, yield 32%). LC-MS (ESI) m/z: 457 (M+1)+.

後処理

  1. additionAfter the addition
  2. customThe mixture was quenched with water (10 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate (100 mL×4)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto give crude product, which
  10. customwas purified by chromatography (silica gel, petroleum ether/ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-804f256ec1a94f4bb8409879c1f3eeca
出典データセット
uspto-grants-2013_04
特許番号
US08420650B2

反応ノート

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